In the worlds of human-computer interaction and interaction design, the most strongly recommended first step is to understand the end users and participants who will be involved with and impacted by the eventual intended experience. There are likely some ways of doing things with technology that have emerged from within research and design communities that could be promising and worthy of importing. This chapter provides two examples, which involves looking at how technologies are used in non-student, non-school-based, body-data collecting communities to inform how to improve learning activities with wearable technologies targeted for students and within schools. The first involves looking to the quantified self-movement to change how wearable technologies were being used in an elementary school classroom. The second involves looking at how and why athletes track their data to get students to rethink their school day recess time.